DNA-Binding Compounds. III. Synthesis of a Peptide-Linked Binuclear Platinum(II)-Terpyridine Complex

Am, Bray; Kelly, DP; Mack, P. O. L.; Martin, RF; Wakelin, Lpg

doi:10.1071/ch9900629

Cited by 4 publications

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“…Reductive amination between N-Boc-δ-aminobutanal 5 16 and crude norheroin 4 using NaBH(OAc) 3 gave Boc-protected amine 6 in 65% yield from heroin hydrochloride 3 . Acidic deprotection of 6 yielded primary amine 7 , which was coupled without purification with trityl-protected thiol 8 17 to give trityl protected heroin hapten 9 in 70% yield from Boc-protected amine 6 . At this point, trityl protected morphine hapten 10 was synthesized in 63% yield from Boc-protected amine 6 by saponification of protected heroin hapten 9 .…”

Section: Resultsmentioning

confidence: 99%

A Vaccine Strategy that Induces Protective Immunity against Heroin

et al. 2011

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Heroin addiction is a wide-reaching problem with a spectrum of damaging social consequences. A vaccine capable of blocking heroin's effects could provide a long-lasting and sustainable adjunct to heroin addiction therapy. Heroin, however, presents a particularly challenging immunotherapeutic target as it is metabolized to multiple psychoactive molecules. To reconcile this dilemma we examined the idea of a singular vaccine with the potential to display multiple drug-like antigens; thus two haptens were synthesized, one heroin-like and another morphine-like in chemical structure. A key feature in this approach is that immunopresentation with the heroin-like hapten is thought to be immunochemically dynamic such that multiple haptens are simultaneously presented to the immune system. We demonstrate the significance of this approach though the extremely rapid generation of robust polyclonal antibody titers with remarkable specificity. Importantly, both the antinociceptive effects of heroin and acquisition of heroin self-administration were blocked in rats vaccinated using the heroin-like hapten.

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Section: Resultsmentioning

confidence: 99%

A Vaccine Strategy that Induces Protective Immunity against Heroin

et al. 2011

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“…Mass spectrum: m / z 157 ({(M − CO 2 − 2H)/2} 2+ , 100%), 243 ({CPh 3 } + , 10%). This compound has been prepared previously by a somewhat different method …”

Section: Methodsmentioning

confidence: 99%

Sulfur Bridging Interactions of Cis-Planar Ni^II−S₂N₂Coordination Units with Nickel(II), Copper(I,II), Zinc(II), and Mercury(II): A Library of Bridging Modes, Including Ni^II(μ₂-SR)₂M^I,IIRhombs

et al. 2004

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Sulfur bridging interactions between three cis-planar NiII-S2N2 complexes and NiII, CuI,II, ZnII, and HgII reactants were investigated by synthesis and X-ray crystal structures of some 24 complexes. This work was stimulated by recent crystallographic structures of the A-cluster of carbon monoxide dehydrogenase/acetylcoenzyme A synthase. This bridged biological assembly has the minimal formulation [Fe4S4]-(micro2-SCys)-[M((micro2-SCys)2Gly)Ni] with M = NiII, CuI, and ZnII at sites distal and proximal, respectively, to the iron-sulfur cluster. Bridges supported by representations of the distal nickel site were sought by reactions of the complexes [NiII(LH-S2N2)]2- and [NiII(LR-S2N2)], with 5-5-5 chelate ring patterns. Reaction products implicate the bridges Ni-(micro2-S)1,2-M in a variety of molecular structures, some with previously unknown connectivities of bridge atoms. The most frequently encountered bridge units are the nonplanar rhombs Ni(2-S)2M involving both sulfur atoms of a given complex. Those with M = NiII are biologically relevant inasmuch as the catalytic metal at the proximal site is nickel. The complex [Ni(L-655)]2-, containing the 6-5-5 ring pattern and coordination sphere of the distal nickel site, was prepared and structurally characterized. It was shown to sustain Ni2(micro2-S)2 rhombic interactions in the form of trinuclear [[Ni(L-655)]2Ni]2- and [[Ni(L-655)]Ni(R2PCH2CH2PR2)] (R = Et, Ph) in which the second NiII simulates the proximal site. Bridging interactions of NiII-S2N2 complexes are summarized, and geometrical features of Ni2(2-S)2 rhombs in these complexes, as dependent on ring patterns, are considered (LH-S2N2 = N,N'-ethylenebis(2-mercaptoisobutyramide)(4-); LR-S2N2 = trans-rac-N,N'-bis(2-mercapto-2-methylprop-1-yl)-1,2-cyclohexanediamine(2-); L-655 = N-(2-mercaptopropyl)-N'-(2'-mercaptoethyl)glycinamide(4-)).

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Platinum complexes of terpyridine: Synthesis, structure and reactivity

Cummings¹

2009

Coordination Chemistry Reviews

115

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DNA-Binding Compounds. III. Synthesis of a Peptide-Linked Binuclear Platinum(II)-Terpyridine Complex

Cited by 4 publications

References 0 publications

A Vaccine Strategy that Induces Protective Immunity against Heroin

A Vaccine Strategy that Induces Protective Immunity against Heroin

Sulfur Bridging Interactions of Cis-Planar Ni^II−S₂N₂Coordination Units with Nickel(II), Copper(I,II), Zinc(II), and Mercury(II): A Library of Bridging Modes, Including Ni^II(μ₂-SR)₂M^I,IIRhombs

Platinum complexes of terpyridine: Synthesis, structure and reactivity

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DNA-Binding Compounds. III. Synthesis of a Peptide-Linked Binuclear Platinum(II)-Terpyridine Complex

Cited by 4 publications

References 0 publications

A Vaccine Strategy that Induces Protective Immunity against Heroin

A Vaccine Strategy that Induces Protective Immunity against Heroin

Sulfur Bridging Interactions of Cis-Planar NiII−S2N2Coordination Units with Nickel(II), Copper(I,II), Zinc(II), and Mercury(II): A Library of Bridging Modes, Including NiII(μ2-SR)2MI,IIRhombs

Platinum complexes of terpyridine: Synthesis, structure and reactivity

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Sulfur Bridging Interactions of Cis-Planar Ni^II−S₂N₂Coordination Units with Nickel(II), Copper(I,II), Zinc(II), and Mercury(II): A Library of Bridging Modes, Including Ni^II(μ₂-SR)₂M^I,IIRhombs